1979
DOI: 10.1073/pnas.76.6.2595
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Intermolecular crosslinking of fatty acyl chains in phospholipids: use of photoactivable carbene precursors.

Abstract: Phospholipids containing photolysable carbene precursors ($l-trifluoro-a-diazopropionoxy and m-diazirinophenoxy groups) in w-positions of sn-2 fatty acyl chains were prepared. Photolysis of their vesicles produced crosslinked products in 40-60% yields. Crosslinking was mostly intermolecular and occurred by carbene insertion into the C-H bonds of a second fatty acyl chain. Crosslinking products were characterized by (i) Photolysis of Vesicles. The sample was introduced into a quartz vessel with a jacket throu… Show more

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Cited by 58 publications
(13 citation statements)
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“…Our observations agree with the notion that aryl nitrenes do not easily insert into C-H bonds [20,23]. We propose that the observed extensive labeling of the platelet phospholipid fraction (see Table I) reflects an addition of the photogenerated nitrene to fatty acid double bonds [11,21].…”
Section: Discussionsupporting
confidence: 90%
“…Our observations agree with the notion that aryl nitrenes do not easily insert into C-H bonds [20,23]. We propose that the observed extensive labeling of the platelet phospholipid fraction (see Table I) reflects an addition of the photogenerated nitrene to fatty acid double bonds [11,21].…”
Section: Discussionsupporting
confidence: 90%
“…27−35 In this context, also azide-modified phospholipids were synthesized. 27,29,30 Although the azide moiety is less reactive than phenylazides and diazirines, 33,36,37 the azide modification has the advantage of less steric hindrance, enhanced stability, and facile incorporation into the fatty acid chain. Hence, it is conceivable that azide-modified lipids cause less disturbance of the lipid bilayer when they are mixed with bilayer-forming phospholipids.…”
Section: ■ Introductionmentioning
confidence: 99%
“…The use of photoreactive membrane lipids to study lipid/peptide interactions is not entirely new. , Khorana et al performed pioneering work on the synthesis of phospholipids containing photoreactive precursors for studying lipid/protein interactions. In this context, also azide-modified phospholipids were synthesized. ,, Although the azide moiety is less reactive than phenylazides and diazirines, ,, the azide modification has the advantage of less steric hindrance, enhanced stability, and facile incorporation into the fatty acid chain. Hence, it is conceivable that azide-modified lipids cause less disturbance of the lipid bilayer when they are mixed with bilayer-forming phospholipids.…”
Section: Introductionmentioning
confidence: 99%
“…Nitrenes, the purported reactive species of azido probes, are very reactive and can undergo a variety of reactions which lead to covalent attachment to neighboring molecules (19). Although there have been reports that azido probes do not insert into phospholipids with saturated fatty acids (4,12), recent work has demonstrated covalent attachment of azido probe derivatives to both intrinsic proteins (5,(16)(17)(18)39) and lipids (5). Studies are under way to determine the specific location of azidopyrene in energized and deenergized E. coli K-12 cells.…”
Section: Discussionmentioning
confidence: 99%